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Vacation rentals with a patio in West Loop, Chicago

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Top-rated accommodations with an outdoor patio in West Loop, Chicago

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Condo in Near West Side

4.86 out of 5 average rating, 99 reviews

Tri-Taylor/Medical Dist. near West Loop

Enjoy this stylish Newly Rehabbed condo equipped with 3 bedrooms and 2 bathrooms. Modern kitchen with stainless steel appliances. ~UNITED CENTER home of the Chicago Bulls and Blackhawks located within 2-3 min walk *2 blocks*. 4-7 min drive to little Italy restaurants/Tri Taylor/Medical District. Near Downtown (5-7min drive). 2 Blocks from the blue line ~Free street parking ~Washer Dryer ~Dishwasher ~spacious Back patio Parties are restricted due to COVID guidelines for the city of Chicago.

Guest favourite

Condo in Chicago

4.91 out of 5 average rating, 64 reviews

Welcome to the Chi! Close to Downtown

Welcome to this contemporary, urban retreat in the bustling heart of River West. This entire unit is thoughtfully designed with modern convenience, catering to those seeking stylish and comfortable accommodation. This trendy unit is in a prime location, just a short walk to the Blue Line and minutes away from 90/94. With an array of restaurants, grocery markets, coffee shops, and stores within walking distance, you'll have the best of Chicago at your doorstep. 5 minute drive to United Center.

Guest favourite

Apartment in Oak Park

4.92 out of 5 average rating, 106 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Guest favourite

Apartment in West Loop

4.97 out of 5 average rating, 37 reviews

Fulton House #1 - Studio Only

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

Guest favourite

Condo in Little Italy

4.96 out of 5 average rating, 123 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favourite

Apartment in Berwyn

4.87 out of 5 average rating, 141 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 178 reviews

Updated Designer Duplex In Fulton Market W/parking

UPDATE: We just completed our luxury renovation March 2023! New kitchen, bathrooms, and patio with a firepit. We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Guest favourite

Condo in West Town

5.0 out of 5 average rating, 102 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Guest favourite

Apartment in Lincoln Park

4.83 out of 5 average rating, 213 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 204 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Apartment in West Town

4.82 out of 5 average rating, 118 reviews

2 Cozy Bedrooms In a Hidden Wicker Park Gem!

Classic and comfortable, my 2-bedroom garden apartment is in the ideal location for any traveler. Just steps from the Blue Line and all the action on Division St and Milwaukee Ave, you'll be in the heart of local favorite neighborhood Wicker Park, while still being able to quickly get downtown to visit the must-see sights. I provide all the essentials to make your stay easy and comfortable! Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

Apartment in Chicago

4.78 out of 5 average rating, 197 reviews

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

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Popular amenities for West Loop, Chicago accommodations with an outdoor patio

Free parking on premises

Air conditioning

Apartment rentals with a patio

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 105 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 188 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

Guest favourite

Apartment in West Lake View

4.93 out of 5 average rating, 100 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Guest favourite

Apartment in Forest Park

4.84 out of 5 average rating, 118 reviews

Home away from home downstairs

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

Chic 1 BR w/Parking, Private Patio

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Fantastic West Loop 2 bedroom

Apartment in West Loop

5.0 out of 5 average rating, 10 reviews

Skyline Oasis: City & Lake Views

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 29 reviews

Wicker Park Walk-Up Condo

House rentals with an outdoor patio

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 32 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 56 reviews

2BD/1 BA with summer patio in quiet Roscoe Village

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 14 reviews

jane's house - a boutique flat in west town -2b/1b

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 89 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 66 reviews

Chicago getaway for two!

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 71 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 12 reviews

Cubby Blue home - Wrigley ~Free Parking~

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Steel and Sky

Condo rentals with a patio

Guest favourite

Condo in Chicago

4.96 out of 5 average rating, 112 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Condo in Chicago

4.82 out of 5 average rating, 188 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Guest favourite

Condo in Lincoln Park

4.96 out of 5 average rating, 104 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 106 reviews

Interior designer duplex 2bd 2bath w/ prvt backyd

Guest favourite

Condo in Chicago

4.82 out of 5 average rating, 310 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Condo in Chicago

4.83 out of 5 average rating, 180 reviews

Can't Beat This 2min Walk to Wrigley!

Guest favourite

Condo in Logan Square

4.95 out of 5 average rating, 129 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Guest favourite

Condo in Chicago

4.94 out of 5 average rating, 36 reviews

Steps from United Center w/ Free Parking near Dwtn

Quick stats about vacation rentals with a patio in West Loop, Chicago

Total rentals
200 properties
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
7.5K reviews

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